4-Methylmorpholine → HCID 178508775, compound

HRID 2365508Notes

Reaction equation

HRID 2365508 reaction equation
Cl.Cl.[NH:3]1[C:7]2([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][NH:5]/[C:4]/1=[N:13]\[C:14]([C:16]1[C:21]([NH2:22])=[N:20][C:19]([NH2:23])=[C:18]([Cl:24])[N:17]=1)=[O:15].[CH2:25]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][C:40](O)=[O:41])=[CH:35][CH:34]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl>[CH2:25]([O:32][C:33]1[CH:34]=[CH:35][C:36]([CH2:39][C:40]([N:10]2[CH2:9][CH2:8][C:7]3([NH:3]/[C:4](=[N:13]/[C:14]([C:16]4[C:21]([NH2:22])=[N:20][C:19]([NH2:23])=[C:18]([Cl:24])[N:17]=4)=[O:15])/[NH:5][CH2:6]3)[CH2:12][CH2:11]2)=[O:41])=[CH:37][CH:38]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 810334-Benzyloxyphenylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178478673HCID 178478673, compound

Product 1

HCID 178508775HCID 178508775, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid [1,3,8-triaza-spiro[4.5]dec-(2E)-ylidene]-amide dihydrochloride (Ex. 38) (300 mg, 0.83 mmol), 4-benzyloxyphenylacetic acid (200 mg, 0.83 mmol), N-methyl morpholine (0.40 ml, 3.64 mmol) and HATU (315 mg, 0.83 mmol) in anhydrous DMF (20 ml) is stirred at room temperature for 16 hours. The reaction mixture is concentrated in vacuo and subjected to column chromatography (basic alumina, 0-3% MeOH in DCM) to obtain pale yellow solid. The product is dissolved in DCM and MeOH and re-precipitated by adding diethyl ether. The supernatant solvent mixture is decanted and the product is washed again with diethyl ether and dried under vacuum to afford the title compound as a pale yellow solid; [M+H]+ 549.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customto obtain pale yellow solid
  3. customMeOH and re-precipitated
  4. additionby adding diethyl ether
  5. customThe supernatant solvent mixture is decanted
  6. washthe product is washed again with diethyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-2497cb75b972450d9fe11b21e7c685ea
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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